Issue 24, 2011
From the journal:

Organic & Biomolecular Chemistry

Sulfonamide carbazole receptors for anion recognition†

Ángel L. Fuentes de Arriba,a   María G. Turiel,a   Luis Simón,ab   Francisca Sanz,c   Juan F. Boyero,d   Francisco M. Muñiz,e   Joaquín R. Morána  and  Victoria Alcázar*f  

* Corresponding authors

a Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, Salamanca, Spain

b Departamento de Ingeniería Química, Universidad de Salamanca, Plaza de los Caídos 1-5, Salamanca, Spain

c Servicio de Rayos X, Universidad de Salamanca, Plaza de los Caídos 1-5, Salamanca, Spain

d Departamento de Química Analítica, Universidad de Salamanca, Plaza de los Caídos 1-5, Salamanca, Spain

e Instituto de Cerámica y Vidrio, CSIC, Kelsen 5, Madrid, Spain

f Departamento de Ingeniería Química Industrial y Medio Ambiente, Universidad Politécnica de Madrid, José Gutiérrez Abascal 2, Madrid, Spain
E-mail: valcazar@etsii.upm.es
Fax: +34 915618618
Tel: +34 913363203

Abstract

Carbazole-based receptors functionalized with two sulfonamide groups have been synthesized and their properties as anion receptors have been evaluated. The receptor with bis(trifluoromethyl)aniline groups has shown a very high affinity for halide ions, especially remarkable as only two hydrogen bonds are formed in the complexes. 1H NMR and fluorescence titrations have been carried out and binding constants up to 7.9 × 106 M−1 have been reached. X-ray structures have been obtained and a modelling study has shown the possible reasons for the large affinity of these compounds for halide anions.

Graphical abstract: Sulfonamide carbazole receptors for anion recognition

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Article information

DOI
https://doi.org/10.1039/C1OB06126G
Article type
Paper
Submitted
08 Jul 2011
Accepted
14 Sep 2011
First published
14 Sep 2011

Org. Biomol. Chem., 2011,9, 8321-8327

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Sulfonamide carbazole receptors for anion recognition

Á. L. Fuentes de Arriba, M. G. Turiel, L. Simón, F. Sanz, J. F. Boyero, F. M. Muñiz, J. R. Morán and V. Alcázar, Org. Biomol. Chem., 2011, 9, 8321 DOI: 10.1039/C1OB06126G

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